Cosmetic and dermatological light protection formulations with a content of benzotriazole derivatives and alkyl naphthalates

ABSTRACT

An active ingredient combination effective for light protection and composed of 
     (a) one or more UV filter substances selected from the group of benzotriazole derivatives and 
     (b) one or more dialkyl naphthalates having the structural formula                    
     in which R 1  and R 2  are, independently of one another, selected from the group of branched and unbranched alkyl groups having 6 to 24 carbon atoms.

The present invention relates to cosmetic and dermatological lightprotection preparations, in particular skin-care cosmetic anddermatological light protection preparations.

The harmful effect of the ultraviolet part of solar radiation on theskin is generally known. The rays have various effects on the skin as anorgan depending on their particular wavelength; so-called UV-C radiationwith a wavelength below 290 nm is absorbed by the ozone layer in theearth's atmosphere and therefore has no physiological significance. Bycontrast, rays in the range between 290 nm and 320 nm, the so-calledUV-B range, cause erythema, simple sunburn or even more or less severebums. The narrower range around 308 nm is stated to be a maximum for theerythema activity of sunlight.

Numerous compounds are known for protecting against UV-B radiation,examples thereof being derivatives of 3-benzylidenecamphor, of4-aminobenzoic acid, of cinnamic acid, of salicylic acid, ofbenzophenone, of 2-phenylbenzimidazole and of s-triazine.

It has long been incorrectly assumed that the long-wavelength UV-Aradiation with a wavelength between 320 nm and 400 nm has only anegligible biological effect. However, it has now¹ been proved by manystudies that UV-A radiation is far more hazardous than UV-B radiation inrelation to the initiation of photodynamic, specifically phototoxic,reactions and chronic changes in the skin. It is also possible for theharmful effect of UV-B radiation to be enhanced by UV-A radiation.

Thus, it has been proved, inter alia, that even UV-A radiation underentirely normal everyday conditions is sufficient to damage within ashort time the collagen and elastin fibers which are of essentialimportance for the structure and firmness of the skin. This results inchronic light-induced skin changes—the skin “ages” prematurely. Theclinical appearance of skin aged by light includes, for example, creasesand wrinkles and an irregular, furrowed relief. In addition, the areasaffected by light-induced skin aging may have irregular pigmentation.The formation of brown spots, keratoses and even carcinomas or malignantmelanomas is also possible. Skin aged prematurely by everyday exposureto UV is additionally distinguished by a lower activity of theLangerhans cells and a slight chronic inflammation.

About 90% of the ultraviolet radiation which reaches the earth consistsof UV-A rays. Whereas UV-B radiation varies greatly depending on a largenumber of factors (for example season and time of day or latitude), UV-Aradiation remains relatively constant from day to day irrespective ofseasonal and diurnal or geographic factors. At the same time, most ofthe UV-A radiation penetrates into living epidermis, while about 70% ofUV-B rays are retained by the stratum corneum.

It is therefore of fundamental importance that cosmetic anddermatological light protection preparations provide adequate protectionboth against UV-B and against UV-A radiation.

In general, the light absorption characteristics of light protectionfilter substances are very well known and documented, especially sincemost industrialized countries have positive lists for the use of suchsubstances, which impose very strict standards on the documentation.

The use concentration of known light protection filter substances is,however, frequently limited in particular in combination with othersubstances present as solids. There are thus certain technicaldifficulties in formulating to achieve higher sun protection factors andeffective UV-A protection.

Advantageous light protection filters are those distinguished by thebenzotriazole structural motif

An advantageous benzotriazole derivative is2,2′-methylenebis(6-(2H-benzotriazol-2-yl)-4-(1,1,3,3-tetramethylbutyl)phenol),which has the chemical structural formula

(INCl: bisoctyltriazole). It is obtainable under the proprietary nameTinosorb® from CIBA-Chemikalien GmbH and is distinguished by good UVabsorption properties. The disadvantage of this substance is thecharacteristic of forming imperceptibly thin films on the skin whichhave unpleasant tactile properties.

Another disadvantage is that such benzotriazole derivatives show onlyinadequate solubility, if any, in conventional oil components.Well-known solvents can dissolve only up to a maximum of 15% by weightof these compounds, which usually corresponds to a concentration ofabout 1 to 1.5% by weight of dissolved (=active) filter substance in thecomplete cosmetic or dermatological preparation.

One disadvantage of the prior art is accordingly that generally onlycomparatively low sun protection factors have been achievable with thesefilter substances because their solubility or dispersibility in theformulations is too low, i.e. they can be satisfactorily incorporatedinto such formulations only with difficulty or not at all.

Even if it is also possible in principle to achieve a certain UVprotection when the solublity is limited, another problem frequentlyoccurs, that is recrystallization.

Substances of low solubility in particular recrystallize comparativelyrapidly, which may be induced by fluctuations in temperature or otherinfluences. Uncontrolled recrystallization of an essential ingredient ofa preparation such as a UV filter has, however, extremelydisadvantageous effects on the properties of the given preparation and,not least, on the desired light protection.

It was an object of the present invention to obtain in a simple mannerpreparations which are distinguished by an increased content ofunsymmetrically substituted triazine derivatives and a correspondinglyhigh sun protection factor.

It was, however, surprising and not predictable for the skilled workerthat the disadvantages of the prior art are remedied by activeingredient combinations effective for light protection and composed of

(a) one or more UV filter substances selected from the group ofbenzotriazole derivatives and

(b) one or more dialkyl naphthalates having the structural formula

in which R¹ and R² are, independently of one another, selected from thegroup of branched and unbranched alkyl groups having 6 to 24 carbonatoms.

Also according to the invention is, in particular, the use of one ormore dialkyl naphthalates having the structural formula

in which R¹ and R² are, independently of one another, selected from thegroup of branched and unbranched alkyl groups having 6 to 24 carbonatoms, as solvent, solution aid, solubilizer or stabilizer forbenzotriazole derivates.

In a particularly advantageous embodiment, the present invention relatesto the use of one or more dialkyl naphthalates having the structuralformula

in which R¹ and R² are, independently of one another, selected from thegroup of branched and unbranched alkyl groups having 6 to 24 carbonatoms, for achieving or increasing the solubility of benzotriazolederivatives in

(a) either an isolated oil component or

(b) at least one oil phase of a disperse two-phase or multiphase systemwhich may additionally comprise one or more aqueous phases.

In another particularly advantageous embodiment, the present inventionrelates to the use of one or more dialkyl naphthalates having thestructural formula

in which R¹ and R² are, independently of one another, selected from thegroup of branched and unbranched alkyl groups having 6 to 24 carbonatoms, for improving the incorporability of benzotriazole derivatives in

(a) either an isolated oil component or

(b) at least one oil phase of a disperse two-phase or multiphase systemwhich may additionally comprise one or more aqueous phases,

It is assumed, especially in the case of benzotriazole derivatives ofparticularly low solubility, that the dialkyl naphthalate(s) display theproperty of forming fine dispersions of such benzotriazole derivatives

(a) either in an isolated oil component or

(b) in at least one oil phase of a disperse two-phase or multiphasesystem which may additionally comprise one or more aqueous phases,better than the components of the prior art were able to do or suggestedthis.

It is preferred according to the invention for the disperse two-phase ormultiphase systems which, besides one or more oil phases, mayadditionally comprise one or more aqueous phases to be constituted inthe form of cosmetic or dermatological emulsions—for example of the W/O,OW, W/O/W or O/W/O type. Such emulsions may preferably also be amicroemulsion, a Pickering emulsion or a sprayable emulsion. It may,however, also be advantageous for the preparations of the invention tobe a solution, a hydrodispersion, an aerosol, a foam or else a stick.

Dialkyl naphthalates advantageous for the purpose of the presentinvention are those where R¹ and/or R² are branched alkyl groups having6 to 10 carbon atoms. Diethylhexyl naphthalate is very particularlypreferred.

Particularly advantageous light protection filters for the purpose ofthe present invention having the benzotriazole structural motif arerepresented by the structure

where R₁ and R₂ are, independently of one another, selected from thegroup of branched or unbranched C₁-C₁₈-alkyl radicals, ofC₅-C₁₂-cycloalkyl or aryl radicals which are optionally substituted byone or more C₁-C₄ alkyl groups.

The preferred benzotriazole derivative is2,2′-methylenebis(6-(2H-benzotriazol-2-yl)-4-(1,1,3,3-tetramethylbutyl)phenol)which is characterized by the chemical structural formula

An advantageous broadband filter for the purpose of the presentinvention is moreover2-(2H-benzotriazol-2-yl)-4-methyl-6-[2-methyl-3-[1,3,3,3-tetramethyl-1-[(trimethyl-silyl)oxy]disiloxanyl]propyl]phenol(CAS No.: 155633-54-8) with the INCl name drometrizole trisiloxane,which is characterized by the chemical structural formula

The total amount of one or more benzotriazole derivatives, in particularof2,2′-methylenebis(6-(2H-benzotriazol-2-yl)-4-(1,1,3,3-tetramethylbutyl)phenol)and/or2-(2H-benzotriazol-2-yl)-4-methyl-6-[2-methyl-3-[1,3,3,3-tetramethyl-1-[(trimethylsilyl)oxy]disiloxa-nyl]propyl]phenol,in the finished cosmetic or dermatological preparations isadvantageously chosen from the range from 0.1 to 15.0% by weight,preferably 0.5 to 10.0% by weight, based on the total weight of thepreparations.

The cosmetic or dermatological light protection formulations of theinvention may have conventional compositions and be used for cosmetic ordermatological light protection and for the treatment, care andcleansing of skin and/or the hair and as a make-up product in decorativecosmetics.

For use, the cosmetic and dermatological preparations are applied to theskin and/or the hair in a sufficient quantity in the manner customaryfor cosmetics.

The cosmetic and dermatological preparations according to the inventioncan comprise cosmetic auxiliaries such as those conventionally used insuch preparations, e.g. preservatives, bactericides, perfumes,antifoams, dyes, pigments which have a coloring effect, thickeners,moisturizers and/or humectants, fats, oils, waxes or other conventionalconstituents of a cosmetic or dermatological formulation, such asalcohols, polyols, polymers, foam stabilizers, electrolytes, organicsolvents or silicone derivatives.

An additional content of antioxidants is generally preferred. Accordingto the invention, favorable antioxidants which can be used are anyantioxidants suitable or conventional for cosmetic and/or dermatologicalapplications.

The antioxidants are particularly advantageously chosen from the groupconsisting of amino acids (e.g. glycine, histidine, tyrosine,tryptophan) and derivatives thereof, imidazoles (e.g. urocanic acid) andderivatives thereof, peptides such as D,L-camosine, D-carnosine,L-carnosine and derivatives thereof (e.g. anserine), carotenoids,carotenes (e.g. α-carotene, β-carotene, lycopene) and derivativesthereof, chlorogenic acid and derivatives thereof, lipoic acid andderivatives thereof (e.g. dihydrolipoic acid), aurothioglucose,propylthiouracil and other thiols (e.g. thioredoxin, glutathione,cysteine, cystine, cystamine and the glycosyl, N-acetyl, methyl, ethyl,propyl, amyl, butyl and lauryl, palmitoyl, oleyl, γ-linoleyl,cholesteryl and glyceryl esters thereof) and salts thereof, dilaurylthiodipropionate, distearyl thiodipropionate, thiodipropionic acid andderivatives thereof (esters, ethers, peptides, lipids, nucleotides,nucleosides and salts) and sulfoximine compounds (e.g. buthioninesulfoximines, homocysteine sulfoximine, buthionine sulfones, penta-,hexa-, heptathionine sulfoximine) in very low tolerated doses (e.g. pmolto μmol/kg), and also (metal) chelating agents (e.g. α-hydroxy fattyacids, palmitic acid, phytic acid, lactoferrin), α-hydroxy acids (e.g.citric acid, lactic acid, malic acid), humic acid, bile acid, bileextracts, bilirubin, biliverdin, EDTA, EGTA and derivatives thereof,unsaturated fatty acids and derivatives thereof (e.g. γ-linolenic acid,linoleic acid, oleic acid), folic acid and derivatives thereof,ubiquinone and ubiquinol and derivatives thereof, vitamin C andderivatives (e.g. ascorbyl palmitate, Mg ascorbyl phosphate, ascorbylacetate), tocopherols and derivatives (e.g. vitamin E acetate), vitaminA and derivatives (vitamin A palmitate) and coniferyl benzoate of gumbenzoin, rutinic acid and derivatives thereof, α-glycosylrutin, ferulicacid, furfurylideneglucitol, carnosine, butylhydroxytoluene,butylhydroxyanisole, nordihydroguaiaretic acid,trihydroxybutyro-phenone, uric acid and derivatives thereof, mannose andderivatives thereof, zinc and derivatives thereof (e.g. ZnO, ZnSO₄),selenium and derivatives thereof (e.g. selenomethionine), stilbenes andderivatives thereof (e.g. stilbene oxide, trans-stilbene oxide) and thederivatives (salts, esters, ethers, sugars, nucleotides, nucleosides,peptides and lipids) of said active ingredients which are suitableaccording to the invention.

The oil phase of the formulations which comprise the substancecombination of the invention is advantageously chosen from the group ofpolar oils, for example from the group of lecithins and fatty acidtriglycerides, namely the glycerol triesters of saturated and/orunsaturated, branched and/or unbranched alkanecarboxylic acids with achain length of from 18 to 24, in particular 12 to 18, C atoms. Thefatty acid triglycerides can, for example, advantageously be chosen fromthe group of synthetic, semisynthetic and natural oils such as, forexample, caprylic/capric triglyceride, cocoa glyceride, olive oil,sunflower oil, soybean oil, peanut oil, rapeseed oil, almond oil, palmoil, coconut oil, castor oil, wheatgerm oil, grapeseed oil, saffloweroil, evening primrose oil, macadamia nut oil and the like.

For the purposes of the present invention, further advantageous polaroil components can also be chosen from the group of esters of saturatedand/or unsaturated, branched and/or unbranched alkanecarboxylic acidswith a chain length of from 3 to 30 C atoms and saturated and/orunsaturated, branched and/or unbranched alcohols with a chain length offrom 3 to 30 C atoms, and from the group of esters of aromaticcarboxylic acids and saturated and/or unsaturated, branched and/orunbranched alcohols with a chain length of from 3 to 30 C atoms. Suchester oils can then be advantageously chosen from the group of octylpalmitate, octyl cocoate, octyl isostearate, octyldodecyl myristate,cetearyl isononanoate, isopropyl myristate, isopropyl palmitate,isopropyl stearate, isopropyl oleate, n-butyl stearate, n-hexyl laurate,n-decyl oleate, isooctyl stearate, isononyl stearate, isononylisononanoate, 2-ethylhexyl palmitate, 2-ethylhexyl laurate, 2-hexyldecylstearate, 2-octyldodecyl palmitate, stearyl heptanoate, oleyl oleate,oleyl erucate, erucyl oleate, erucyl erucate, tridecyl stearate,tridecyl trimellitate, and synthetic, semisynthetic and natural mixturesof such esters such as, for example, jojoba oil.

The oil phase can advantageously also be chosen from the group ofdialkyl ethers, an advantageous example being dicaprylyl ether.

It is also preferred to choose the oil component(s) from the group ofisoeicosane, neopentyl glycol diheptanoate, propylene glycoldicaprylate/dicaprate, caprylic/capric/diglyceryl succinate, butyleneglycol caprylate/caprate, C₁₂₋₁₃-alkyl lactate, di-C₁₂₋₁₃-alkyltartrate, tri-isostearin, dipentaerythrityl hexacaprylate/hexacaprate,propylene glycol monoisostearate, tricaprylin, dimethylisosorbide. It isparticularly advantageous if the oil phase in the formulations of theinvention has a content of C₁₂₋₁₅-alkyl benzoate or consists entirely ofthe latter.

Any mixtures of such oil and wax components can also be advantageouslyemployed for the purpose of the present invention.

The oil phase may likewise advantageously also contain nonpolar oils,for example those selected from the group of branched and unbranchedhydrocarbons and waxes, in particular mineral oil, Vaseline(petrolatum), liquid paraffin, squalane and squalene, polyolefins,hydrogenated polyisobutenes and isohexadecane. The preferred substancesamong polyolefins are polydecenes.

The oil phase may also advantageously have a content of cyclic or linearsilicone oils or consist completely of such oils, it being preferred,however, to use besides the silicone oil or silicone oils an additionalcontent of other oil phase components.

Cyclomethicone (octamethylcyclotetrasiloxane) is advantageously employedas silicone oil to be used according to the invention. However, othersilicone oils can also advantageously be used for the purpose of thepresent invention, for example cetyldimethicone,hexamethyl-cyclotrisiloxane, polydimethylsiloxane,poly(methylphenylsiloxane).

Also advantageous according to the invention are, for example, naturalwaxes of animal and plant origin, such as, for example, beeswax, chinesewax, bumblebee wax and other insect waxes, and shea butter.

The aqueous phase of the preparations of the invention mayadvantageously comprise conventional cosmetic auxiliaries such as, forexample, alcohols, in particular those of low C number, preferablyethanol and/or isopropanol, diols or polyols of low C number, and ethersthereof, preferably propylene glycol, glycerol, ethylene glycol,ethylene glycol monoethyl or monobutyl ether, propylene glycolmonomethyl, monoethyl or monobutyl ether, diethylene glycol monomethylor monoethyl ether and analogous products, polymers, foam stabilizers,electrolytes and, in particular, one or more thickeners which mayadvantageously be chosen from the group of silicon dioxide, aluminumsilicates, polysaccharides and derivatives thereof, for examplehyaluronic acid, xanthan gum, hydroxypropylmethylcellulose, particularlyadvantageously from the group of polyacrylates, preferably apolyacrylate from the group of so-called carbopols, for examplecarbopols of types 980, 981, 1382, 2984, 5984, in each case singly or incombination. Moisturizers can also preferably be used.

Substances or mixtures of substances referred to as moisturizers arethose which confer on cosmetic or dermatological preparations theproperty of reducing the moisture loss from the stratum corneum (alsocalled the transepidermal water loss) (TEWL)) and/or have a beneficialeffect on the hydration of the stratum corneum, after application ordispersion on the surface of the skin.

Advantageous moisturizers for the purpose of the present invention are,for example, glycerol, lactic acid, pyrrolidonecarboxylic acid and urea.It is also particularly advantageous to use polymeric moisturizers fromthe group of polysaccharides which are soluble in water and/or swellablein water and/or gellable using water. Particularly advantageous are, forexample, hyaluronic acid, chitosan and/or a fucose-rich polysaccharidewhich is listed in Chemical Abstracts under the registry number178463-23-5 and is obtainable, for example, under the name Fucogel®1000from SOLABIA S.A.

According to their constitution, cosmetic or topical dermatologicalcompositions can be used for the purpose of the present invention forexample as skin protection cream, cleansing milk, day or night creametc. It is possible and advantageous where appropriate to use thecompositions of the invention as the basis for pharmaceuticalformulations.

Cosmetic and dermatological preparations in the form of a sunscreencomposition are also beneficial. These preferably comprise in additionto the active ingredient combinations of the invention additionally atleast one other UV-A filter substance and/or at least one other UV-Bfilter substance. Formulations of these types may, although notnecessarily, where appropriate also comprise one or more inorganicpigments as UV filter substances.

Preferred inorganic pigments are based on metal oxides and/or othermetal compounds which have low solubility or are insoluble in water, inparticular the oxides of titanium (TiO₂), zinc (ZnO), iron (for exampleFe₂O₃), zirconium (ZrO₂), silicon (SiO₂), manganese (for example MnO),aluminum (Al₂O₃), cerium (for example Ce₂O₃), mixed oxides of thecorresponding metals, and mixtures of such oxides.

An additional content of titanium dioxide and/or zinc oxide particleswith a stabilizing effect may, of course, also be advantageous but isnot necessary for the purpose of the present invention.

It is also advantageous for the purpose of the present invention todesign cosmetic and dermatological preparations whose main purpose isnot to protect from sunlight but nevertheless comprise a content ofUV-protective substances. Thus, for example, it is usual to incorporateUV-A and UV-B filter substances into day creams.

UV-protective substances as well as antioxidants and, if required,preservatives also represent effective protection of the preparationsthemselves against spoilage.

Preparations of the invention preferably comprise substances whichabsorb UV radiation in the UV-A and/or UV-B range, the total amount ofthe filter substances being, for example, 0.1% by weight to 30% byweight, preferably 0.5 to 20% by weight, in particular 1.0 to 15.0% byweight, based on the total weight of the preparations, in order toprovide cosmetic preparations which protect the hair or the skin fromthe entire range of ultraviolet radiation. They may also act assunscreen compositions for the hair or the skin.

If the emulsions of the invention comprise UV-B filter substances, thesemay be oil-soluble or water-soluble. Examples of oil-soluble UV-Bfilters advantageous according to the invention are:

3-benzylidenecamphor derivatives, preferably3-(4-methylbenzylidene)camphor, 3-benzylidenecamphor;

4-aminobenzoic acid derivatives, preferably 2-ethylhexyl4-(dimethylamino)benzoate, amyl 4-(dimethylamino)benzoate;

esters of cinnamic acid, preferably 2-ethylhexyl 4-methoxycinnamate,isopentyl 4-methoxycinnamate;

esters of salicylic acid, preferably 2-ethylhexyl salicylate,4-isopropylbenzyl salicylate, homomenthyl salicylate,

derivatives of benzophenone, preferably 2-hydroxy-4-methoxybenzophenone,2-hydroxy-4-methoxy-4′-methylbenzophenone,2,2′-dihydroxy-4-methoxybenzophenone;

esters of benzalmalonic acid, preferably di(2-ethylhexyl)4-methoxybenzalmalonate,

triazine derivatives symmetrical in relation to the C₃ axis of the basictriazine, preferably4,4′,4″-(1,3,5-triazin-2,4,6-triyltriimino)trisbenzoic acidtris(2-ethylhexylester) [INCl: octyl triazone], which is marketed byBASF Aktiengesellschaft under the trade name UVINUL® T 150,

and UV filters bound to polymers.

Examples of advantageous water-soluble UV-B filters are:

salts of 2-phenylbenzimidazole-5-sulfonic acid such as its sodium,potassium or its triethanolammonium salt, and the sulfonic acid itself;

sulfonic acid derivatives of benzophenones, preferably2-hydroxy-4-methoxybenzo-phenone-5-sulfonic acid and its salts;

sulfonic acid derivatives of 3-benzylidenecamphor such as, for example,4-(2-oxo-3-bornylidenemethyl)benzenesulfonic acid,2-methyl-5-(2-oxo-3-bornylidenemethyl)-benzenesulfonic acid and theirsalts.

The list of UV-B filters mentioned which may be used in the preparationsof the invention is, of course, not intended to be limiting.

Advantageous UV filter substances for the purpose of the presentinvention are in addition so-called broadband filters, i.e. filtersubstances which absorb both UV-A and UV-B radiation.

It may also be advantageous to use in preparations of the invention UV-Afilters which have to date normally been present in cosmeticpreparations. These substances are preferably derivatives ofdibenzoylmethane, in particular1-(4-tert-butylphenyl)-3-(4-methoxyphenyl)-propane-1,3-dione and1-phenyl-3-(4-isopropylphenyl)propane-1,3-dione.

It may also be advantageous to add, in addition to the ingredientsessential to the invention, further asymmetrically substituteds-triazine derivatives, for example those described in EP-A-570 838,whose chemical structure is represented by the generic formula

where

R is a branched or unbranched C₁-C₁₈-alkyl radical, a C₅-C₁₂-cycloalkylradical, optionally substituted by one or more C₁-C₄-alkyl groups, and

X is an oxygen atom or an NH group,

R₁ is a branched or unbranched C₁-C₁₈-alkyl radical, a C₅-C₁₂-cycloalkylradical, optionally substituted by one or more C₁-C₄-alkyl groups, or ahydrogen atom, an alkali metal atom, an ammonium group or a group of theformula

in which

A is a branched or unbranched C₁-C₁₈-alkyl radical, a C₅-C₁₂-cycloalkylor aryl radical, optionally substituted by one or more C₁-C₄-alkylgroups,

R₃ is a hydrogen atom or a methyl group,

n is a number from 1 to 10,

R₂ is a branched or unbranched C₁-C₁₈-alkyl radical, a C₅-C₁₂-cycloalkylradical, optionally substituted by one or more C₁-C₄-alkyl groups, and

if X is the NH group,

a branched or unbranched C₁-C₁₈-alkyl radical, a C₅-C₁₂-cycloalkylradical, optionally substituted by one or more C₁-C₄-alkyl groups, or ahydrogen atom, an alkali metal atom, an ammonium group or a group of theformula

in which

A is a branched or unbranched C₁-C₁₈-alkyl radical, a C₅-C₁₂-cycloalkylor aryl radical, optionally substituted by one or more C₁-C₄-alkylgroups,

R₃ is a hydrogen atom or a methyl group,

n is a number from 1 to 10, if X is an oxygen atom.

Particularly advantageous asymmetrically substituted s-triazines arethose selected from the group of substances described in EP-A-775 698:

All the bisresorcinyltriazines mentioned in this publication whetherdisclosed by generic or by specific formulae, are advantageous for thepurpose of the present invention. R₄ and R₅ are very particularlyadvantageously selected from the group of branched or unbranched alkylgroups of 1 to 18 carbon atoms. The alkyl groups may also againadvantageously be substituted by silyloxy groups.

A₁ is advantageously a substituted homocyclic or heterocyclic aromaticfive-membered ring or six-membered ring.

The following compounds are very particularly advantageous:

where R₆ is a hydrogen atom or a branched or unbranched alkyl group with1 to 10 carbon atoms, in particular2,4-bis{[4-(2-ethylhexyloxy)-2-hydroxy]phenyl}6-(4-methoxyphenyl)-1,3,5-triazine(INCl: aniso triazine), which is obtainable under the proprietary nameTinosorb® S from CIBA-Chemikalien GmbH and is characterized by thefollowing structure:

It is also advantageous where appropriate to provide preparations of theinvention with a content of2,4-bis{[4-(3-sulfonato-2-hydroxypropyloxy)-2-hydroxy]phenyl}-6-(4-methoxyphenyl)-1,3,5-triazinesodium salt, which is characterized by the following structure:

It is also advantageous where appropriate to provide preparations of theinvention with a content of2,4-bis{[4-(3-(2-propyloxy)-2-hydroxypropyloxy)-2-hydroxy]phenyl}-6-(4-methoxyphenyl)-1,3,5-triazine,which is characterized by the following structure:

It is also advantageous where appropriate to provide preparations of theinvention with a content of2,4-bis{[4-(2-ethylhexyloxy)-2-hydroxy]phenyl}-6-[4-(2-methoxyethoxycarbonyl)-phenylamino]-1,3,5-triazine,which is characterized by the following structure:

It is also advantageous where appropriate to provide preparations of theinvention with a content of2,4-bis{[4-(3-(2-propyloxy)-2-hydroxypropyloxy)-2-hydroxy]phenyl}6-[4-(ethoxycarbonyl)phenylamino]-1,3,5-triazinewhich is characterized by the following structure:

It is also advantageous where appropriate to provide preparations of theinvention with a content of2,4-bis{[4-(2-ethylhexyloxy)-2-hydroxy]phenyl}-6-(1-methylpyrrol-2-yl)-1,3,5-triazine,which is characterized by the following structure:

It is also advantageous where appropriate to provide preparations of theinvention with a content of2,4-bis{[4-tris(trimethylsiloxysilylpropyloxy)-2-hydroxy]phenyl}-6-(4-methoxyphenyl)-1,3,5-triazine,which is characterized by the following structure:

It is also advantageous where appropriate to provide preparations of theinvention with a content of2,4-bis{[4-(2-methylpropenyloxy)-2-hydroxy]phenyl}-6-(4-methoxyphenyl)-1,3,5-triazine,which is characterized by the following structure:

It is also advantageous where appropriate to provide preparations of theinvention with a content of2,4-bis{[4-(1′,1′,1′,3′,5′,5′,5′-heptamethylsiloxy-2-methylpropyloxy)-2-hydroxyl]-phenyl}-6-(4-methoxyphenyl)-1,3,5-triazine,which is characterized by the following structure:

It is also advantageous where appropriate to provide preparations of theinvention with a content of an asymmetrically substituted s-triazinewhose chemical structure is represented by the formula

which is also referred to hereinafter as dioctylbutylamidotriazone(INCl) and is obtainable under the proprietary name UVASORB HEB fromSigma 3V.

The symmetrically or asymmetrically substituted s-triazine derivative(s)are, if their presence is desired, advantageously incorporated into theoil phase of the cosmetic or dermatological formulations.

Further advantageous UV-A filter substances are1,4-bis(4,6-disulfo-2-benzimidazolyl)benzene:

and its salts, especially the corresponding sodium, potassium ortriethanolammonium salts, in particular1,4-bis(4,6-disulfo-2-benzimidazolyl)benzene disodium salt:

and 1,4-bis(2-oxo-10-sulfo-3-bornylidenemethyl)benzene and it salts(especially the corresponding 10-sulfonato compounds, in particular thecorresponding sodium, potassium or triethanolammonium salt), which isalso referred to as benzene-1,4-di(2-oxo-3-bornylidenemethyl-10-sulfonicacid) and which has the following structure:

The invention also relates to preparations comprising UV-A filters. Theamounts used for the UV-B combination can be employed.

It may also be advantageous where appropriate to incorporate accordingto the invention further UV-A and/or UV-B filters into cosmetic ordermatological preparations, for example particular salicylic acidderivatives such as 4-isopropylbenzyl salicylate, 2-ethylhexylsalicylate (=octyl salicylate), homomenthyl salicylate.

Another light protection filter substance advantageously to be usedaccording to the invention is ethylhexyl 2-cyano-3,3-diphenylacrylate(octocrylene), which is obtainable from BASF under the name Uvinul® N539, and which has the following structure:

The list of UV filters mentioned, which can be employed for the purposeof the present invention, is, of course, not intended to be limiting.

The following examples are intended to illustrate the present inventionwithout restricting it. The numerical values in the examples meanpercentages by weight based on the total weight of the respectivepreparations.

Example 1 Example 2 Example 3 Example 4 Example 5 O/W 1 O/W 2 W/O 1 W/O2 W/O 3 Stearic acid 1.50 — — — — Glycerol monostearate 3.00 — — — —Sorbitan stearate —  3.00 — — — Polyglyceryl-3-methylglucose distearate—  1.50 — — — Polyglyceryl-2 dipolyhydroxystearate — — 5.00 — — Cetyldimethicone copolyol — — — — 5.00 PEG-30 dipolyhydroxystearate — — — 4.00 — Dimethicone 2.00 — 2.00 — 5.00 Phenyltrimethicone 2.00 — —  5.003.00 Vitamin E acetate 0.50  0.50 —  0.50 — Drometrizole trisiloxane3.00 — 3.00 — 5.00 Bisoctyltriazole —  3.00 2.00  5.00 2.00 AerosilR972 ® — — —  0.50 — Hailbrite TQ ® 6.00  8.00 5.00  4.00 7.00Preservative 0.50  0.50 0.50  0.50 0.50 Glycerol 3.00 10.00 5.00 10.005.00 MgSO₄ — — 1.00  1.00 — NaCl — — — — 1.00 Xanthan gum 0.30 — — — —Pemulen TR1 ® —  0.10 — — — 45% Sodium hydroxide solution 0.50  1.20 — —1.30 Water ad 100.00 ad 100.00 ad 100.00 ad 100.00 ad 100.00 Example 6Example 7 Example 8 Example 9 ydrodispersion W/O Pickering emulsionSpray Spray Glycerol monostearate — —  4.00 — Glycerol monostearate SE —— — 4.50 Ceteareth-20 — — — 1.00 Ceteareth-12 — —  1.50 — Dimethicone —— — 2.00 Phenyltrimethicone — 5.00 — — Vitamin E acetate — 0.50 — —Drometrizole trisiloxane 2.00 5.00 — 2.00 Bisoctyltriazole 2.00 5.00 2.00 — Eusolex T2000 ® — 4.00 — — Aerosil R972 ® — 1.00 — — HallbriteTQ ® 8.00 4.00  5.00 6.00 Preservative 0.50 0.50  0.50 0.50 Glycerol —3.00 10.00 5.00 Xanthan gum 0.50 — — — Pemulen TR1 ® 0.30 — — — 45%Sodium hydroxide 0.30 —  0.40 — solution Water ad 100.00 ad 100.00 ad100.00 ad 100.00

What is claimed is:
 1. A cosmetic or dermatological compositioneffective for light protection, which is comprised of (a) one or morebenzotriazole UV filter compounds; and (b) one or more dialkylnaphthalates having the structural formula

in which R¹ and R² are, independently of one another, branched orunbranched alkyl groups having 6 to 24 carbon atoms.
 2. The compositionof claim 1, wherein the dialkyl naphthalate is diethylhexyl naphthalate.3. The composition of claim 1, wherein the benzotriazole UV filtercompound has the structure

where R₁ and R₂ are, independently of one another, selected from thegroup consisting of branched or unbranched: (a) C₁-C₁₈-alkyl radicals;(b) C₅-C₁₂-cycloalkyl or aryl radicals; wherein said R₁ and R₂ areoptionally substituted by one or more C₁-C₄-alkyl groups.
 4. Thecomposition of claim 1, wherein the benzotriazole UV filter compound hasthe structure


5. The composition of claim 1, wherein the the benzotriazole UV filtercompound has the structure


6. A method of solubilizing or stabilizing a benzotriazole compoundwhich comprises of adding a solubilizing or stabilizing effective amountof one or more dialkyl naphthalates having the structural formula

in which R¹ and R² are, independently of one another, branched orunbranched alkyl groups having 6 to 24 carbon atoms to saidbenzotriazole compound.
 7. A method of solubilizing or increasing thesolubility of a benzotriazole compound in: (a) an isolated oilcomponent; or (b) at least one oil phase of a disperse two-phase ormultiphase system which optionally comprises of one or more aqueousphases, which comprises of adding a solubilizing or stabilizingeffective amount of one or more dialkyl naphthalates having thestructural formula:

in which R¹ and R² are, independently of one another, branched orunbranched alkyl groups having 6 to 24 carbon atoms, to saidbenzotriazole compound.
 8. A method of improving the incorporation of abenzotriazole compound in either: (a) an isolated oil component; or (b)at least one oil phase of a disperse two-phase or multiphase systemwhich may additionally comprise one or more aqueous phases, whichcomprises of adding an incorporation improving amount of one or moredialkyl naphthalates having the structural formula

in which R¹ and R² are, independently of one another, branched andunbranched alkyl groups having 6 to 24 carbon atoms, to saidbenzotriazole compound.
 9. A method of protecting the skin from UV lightwhich comprises of administering to a patient in need thereof aneffective amount of the composition of claim 1.